Triethylamine → 3-(Chloromethyl)-2-methylpyridine

HRID 1901082Notes

Reaction equation

HRID 1901082 reaction equation
O[CH2:2][C:3]1[C:4]([CH3:9])=[N:5][CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.CS([Cl:21])(=O)=O>C1C=CC=CC=1>[Cl:21][CH2:2][C:3]1[C:4]([CH3:9])=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 302564(2-Methylpyridin-3-yl)methanol

Product 1

HCID 122437113-(Chloromethyl)-2-methylpyridine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 3-hydroxymethy-2-methylpyridine (0.65 g, 5.3 mmol) in dry benzene (5 ml) was added triethylamine (1.0 ml, 7.4 mmol) followed by methanesulfonyl chloride (0.78 ml, 10.1 mmol) dropwise over 5 min. The heterogeneous dark gummy mixture was stirred at room temp. overnight. The reaction was filtered through Celite and washed with benzene (2×). The combined filtrates were washed with brine, dried (Na2SO4), and concentrated in vacuo to the crude product as a yellow oil which was used as is.

Workup

  1. filtrationThe reaction was filtered through Celite
  2. washwashed with benzene (2×)
  3. washThe combined filtrates were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo to the crude product as a yellow oil which

Sources & evidence

ORD record
ord-734fc2142b084750aa58313fca5e81ad
Source dataset
uspto-grants-1996_11
Patent number
US05576313

Reaction notes

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